Orthooxyazo dyes



UNITED STATES PATENT. orrlca.

wmnnmm nnnz'nnne, or BERLIN-WILMERSDORF, AND OSWALD scmnrnnnane, or BEnLm-scnon'mm, GERMANY, ASSIGNORS 'roacrmn ensmsnscnerr mm mun runma'non, or BERLIN, GERMANY.

oarnooxxa'zo DYES.

No Drawing.

To all whom it may concern.

Be it known that We, WILHELM HERZBERG and OSWALD SGHARFENBERG, citizens of the German Republic, residing at Berlin-Wilmersdorf, Germany, and Berlin-Schoneberg, Germany, our P. 0. addresses being Prinzregentenstr. 10, Berlin-Wilmersdorf, Ger 12, Berlin-.

many, and ltosenheimerstr. Schoneberg, Germany, have invented certain new and useful Improvements in Orthooxyazo Dyes (for-Which we have made application in ermany Jan. 8, 1920, and Oct. 27, 1920,) of which the following is a specification.

Our present invention relates to new orthooxyazo' dyes whichmay be obtained by combining a polyhalogen-2-diazo-1-oxyderivative of the benzene series with an acidylaminooxynaphthalenesulfonic acid. These new dyes form in the dry pulverized stateof their sodium salts dark powders soluble in water with blue to violet color, the aqueous solution becoming more reddish by addition of sodium carbonate and red by addition of sodium hydroxide, by an acid a violet-red precipitate being separated.

The new dyes when dyed in the presence of an alkali metal chromate and an ammonium' salt, such as ammonium sulfate, furnish on Wool blue tints of an excellent fastness to the action of light, to washing and to milling; the 'same shades being obtained by dyeing on wool mordanted with a chromium'mordant or by dyeing wool in an acid bath and treating these tints afterwards with a chromium mordant. In .order to illustrate our invention the following examples are given, the parts being by weight:

1. 21.3 parts of 3.4.5-trichloro-2-amino-1- oxybenzene. are diazotised by means of 6.9 parts of sodium nitrite and 50 parts of hydrochloric acid of 12 B. specific gravity. The diazo compound is allowedto run into a solution of 28.1 parts of 1-acetylamino-8- oxynaphthalene 4 sulfonic acid, alkaline with sodium carbonate. The dyestuff is salted out and worked up as usual. It dyes wool with chromium mordants blue tints of an excellent fastness.

2. The diazo-compound of 21.3 parts of 3.4.6-trichloro-2-amino-l-oxybenzene is coupled with 39.3 parts of l-toluol-sulfamino- 8 oxynaphthalehei-sulfonic acid'in a solution containing sodium carbonate. The dyestuif Specification of Letters Patent. Patented Feb, 28,1922, Application filed November 5,1921. Serial No. 513,171.

separated in the usual manner dyes wool with chromium mordants blue tints.

3. The diazo compound 'of 19.2 parts of 4-methyl-3.5-dichloro-2-amino-1 oxybenzene is united with a solution of 28.1 parts of. 1 acetylamino8-oxynaphthalene 4; sulfonic acid, alkaline with sodium carbonate. The dye is worked up in the usual manner; it dyes on wool with chromium mordants reddish blue tints.

It is obvious to all skilled in the art that our present invention is not limited to the foregoing examples nor to the details given therein.

What we claim is,-

1. The new ortho-oxyazo dyes which form in the dry pulverized shape of their sodium salts dark powderssoluble in water with blue to violet color, from which an acid separates a violet-red precipitate, the aqueous solution becoming more reddish by addition of sodium carbonate and red by adtion of sodium. hydroxide, yielding upon reduction a polyhalogen-2-amino-l-oxy-derivative of the benzene series and a monoacidyl-diaminooxynaphthalene-sulfonic acid, dyeing on wool in the presence of an alkali metal chromate and an ammonium salt, such as ammonium sulfate, blue tints of an excellent fastness, the same shades being obtained by dyeing on wool mordanted with chromium mordants or by dyeing wool in an acid bath and treating them afterwards with chromium mordants, these dyes which may be obtained by combining a polyhalogen-2-diazo-l-oxyderivative of the bezene series with an. acidyl-amino-oxynaphthalene-sulfonic acid.

2. The new ortho-oxyazo d es which form in the dry shape'of their so ium salts dark powders soluble in water with blue to violet color, from which an acid separates a violetred precipitate, the aqueous solution becoming more reddish by addition of sodium hydroxide, yielding upon reduction a polyhalogen-2-amino-1 -oxybenzene andv a monoacidyldiamino-oxynaphthalene-sulfonic acid dyeing on wooli'n the presence of an alkali metal chromate and an, ammonium salt,

such as ammonium sulfate, blue tints of an excellent fastness, the same shades being obtained by dyeing on.wool mordanted. with chromium mordants or by dyeing wool in an acid bath and treating them afterwards with chromium mordants, these dyes which may be obtained by combining a polyhalogen-2- diazo-l-oxybenzene with an 1-acidylamino- 8-oxynaphthalene-sulfonic acid.

3. The new ortho-oxyazo dyes which form in the dr pulverized shape of their sodium salts dar powders soluble in water with blue to violet color from which an acid separates a violet redprecipitate, the aqueous solution becoming more of sodium carbonate and red by addition of sodium hydroxide yielding upon reduction a polychloro-2-amino-l-oxybenzene and 1- acidylamino 7 amino 8-oxynaphthalene-4csulfonic acid, dyeing on wool in the presence of an alkali metal chromate and an ammonium salt, such as ammonium sulfate, blue' of sodium carbonate and red by addition of sodium hydroxide yielding upon reduction a trichloro-Q-amino-l-oxybenzene and 1- acidylamino 7 amino- 8 -oxynaphthalene-5-.

sulfonic acid, dyeing on wool in the presence of an alkali metal chromate and an ammonium salt, such as ammonium sulfate, blue tints of an excellent fastness, the sameshades being obtained by dyeing on wool mordanted with chromium mordantsor by dyeing wool in an acid bath and treating them afterwards with chromium mordants, these dyes which may be obtained by combining a trichloro-2- diazo-l-oxybenzene with l-acidylamino-S- oxynaqpkhthalenei-sulfonic acid.

e new orthooxy-azo dyes which form in the dry-pulverized shape of their sodium salts dark powders soluble in water with blue to violet color, from which an acid separates a violet-red precipitate, the aqueous solution becoming more reddish by addition of sodium carbonate and red by addition of sodireddish by addition um-hydroxide, yielding upon reduction a trihloro-Q-amino-l-oxybenzene and l-acetylamino-7-amino-8 oxynapthalene 4 sulfonic acid, dyeing on wool in the presence of an alkali metal chromate and an ammonium salt, such as ammonium sulfate, blue'tints of an excellent fastness, the same shades being obtained by dyeing on wool mordanted with chromium mordants or by dyeing wool in an acid bath and treating them afterwards with chromium mordants, these dyes which may be obtained by combining a trichloro-2- diazo-l-oxybenzene with 1 acetylamino-8-- oxynaphthalenei-sulfonic acid.

'6. The new ortho-oxyazo dye which forms in the dry pulverized shape of its sodium salt a dark powder soluble in water with blue color from which an acid separates a violetred precipitate, the aqueous solution becoming more reddish by addition of sodium carbonate and yellowish-red by addition .of sodium-hydroxide, yielding upon reduction 7 3.4.6-trichloro-2-amino-l-oxybenzene and 1- acetylaminm 7 -amino 8 oxynaphthalene-4- sulfonic acid, dying on wool in the presence of an alkali'metalchromate and an ammonium salt, such as ammonium sulfate, blue tints of an excellent fastness, the same shades being obtained by dyeing on wool mordanted with chromium mordants or by dyeing wool in an acid bath and treating them adfterwa'rds with chromium mordants', this dye which 35 may be obtained by combining 3.4.6-trichloro-2-diazo-l-oxybenzene with "l-acetylamino-8-oxynaphthalene-4-sulfonic acid and which corresponds as free acid tothe formula: 9o

:005, on n; NH o1 /N=N c1 k Cl OIH In testimony whereof we afiix our 'signatures in resence of two witnesses.

ILHELM HERZBERG. OSWALD SCHABFENBERG. Witnesses:

MAX BRAUM WALTER D. IJJANVIER. 

